Rent Luxury Accommodation for Groups in Shelter Island

We selected the 920 homes worth renting in this location

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Age 13+

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Age 1 to 12

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Home spotlights in Shelter Island

Divine Inspiration

Divine Inspiration

  • 10 guests

  • 4 bedrooms

Great Barrington, Lee

There are a lot of adjectives we could throw at this home in The Berkshires; cosy, darling, divine. But none of them really do it justice.

The Great Frontier

The Great Frontier

  • 4 guests

  • 1 bedrooms

Chatham, New York

Reminiscent of something from a Laura Ingalls Wilder novel, this picturesque cabin is a haven surrounded by peace and quiet and lush woodland. Although you can count on a serene stay here, you’re also just a five-minute drive from the quaint town of Old Chatham where you can find some local amenities, or a ten-minute drive from Chatham Town, which has several excellent restaurants and plenty of charming local shops.

Long Point

Long Point

  • 8 guests

  • 4 bedrooms

Noyack, Southampton

Set within an acre of lush green grounds, this seriously charming home is just a twenty-minute drive from the centre of Sag Harbour - undoubtedly one of New York State's best-kept secrets. This centuries-old seaside village may be known as one of the most family-friendly places in the Hamptons, but its strictly adults-only activities include a visit to the nearby Wölffer Estate vineyards to sample their famed rosé cider.

Villa Menantic

Villa Menantic

  • 8 guests

  • 4 bedrooms

Shelter Island Heights, Shelter Island

Set across seven private acres on Shelter Island’s Menantic Peninsula, this waterside property epitomises tranquillity. Wake up to views on one of the home's two private balconies, before whipping up breakfast in the state-of-the-art kitchen and sipping your morning coffee as you paddle in the sea.


We selected the top 3% holiday homes in Shelter Island Accommodation for Groups

Explore the 920 most perfect homes in our collection

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Most popular homes in Shelter Island

Cruising The Coast

Cruising The Coast

  • 6 guests

  • 3 bedrooms

Sag Harbor, Southampton

Seascape

Seascape

  • 8 guests

  • 5 bedrooms

Noyack, Southampton

Lake of Beauty

Lake of Beauty

  • 8 guests

  • 4 bedrooms

Columbia County, Livingston

Gift of the Sea

Gift of the Sea

  • 6 guests

  • 2 bedrooms

Nantucket County, Massachusetts

Borne Back

Borne Back

  • 6 guests

  • 3 bedrooms

Northwest Harbor, East Hampton

The Old Life-Saving Station

The Old Life-Saving Station

  • 13 guests

  • 6 bedrooms

East Marion, North Fork

Long Island Iced Tea

Long Island Iced Tea

  • 8 guests

  • 3 bedrooms

Remsenburg, Remsenburg-Speonk

Where the Wind Blows

Where the Wind Blows

  • 8 guests

  • 4 bedrooms

Noyack, Southampton

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Frequently asked questions

Reserve a stay in one of the impeccable homes in our collection of luxury Group Holiday Accommodation in Shelter Island. You won't find such consistent quality anywhere else, as every single Plum Guide home comes fully furnished with all linens, a brilliantly-equipped kitchen, and essential bathroom toiletries included. Our experts really do obsess over the smallest details, with shower pressure and a bedroom's decibel levels being tested to ensure absolute quality in your hunt for the perfect home. Rent Shelter Island Accommodation for Groups today, and learn the true meaning of luxury. Call on our team of experts too, who can help you through the booking process and guarantee that you end up with the ultimate home for you.

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